Sitting in a house on a hill in Tuscany, Italy, watching the sun set and listening to the sound of music coming from the house in which I was staying almost rent-free, I wondered how I had gotten this lucky.

Actually, it was really all thanks to one website—Workaway.info.

Workaway

Workaway is a site that sets travelers up with hosts, who provide visitors with room and board in exchange for roughly five hours of work each weekday. The arrangement varies from host to host—some offer money, others require it—but typically, the Workaway experience is a rare bird: a largely anti-capitalist exchange.

I did four Workaways the summer I traveled in Europe, and then one at a monastery near my home in New York the summer after. Each experience, though they lasted around two weeks each, was among the most enriching times of my life—and I'd argue I learned almost as much through those experiences as I did in four years of college.

There's something extremely special about the Workaway experience, though it's certainly not for everyone.

Workaway Isn't for Everyone: What to Know Before You Go

I loved all the Workaways I went on, but the best advice I can give to anyone considering going is: Enter with an open mind. If you're someone who doesn't do well with the unexpected, if you're not willing to be flexible, if you're a picky eater or easily freaked out, then it's likely that you won't have a good experience at a Workaway.

There are exceptions to all of this. At the Workaway I stayed at in Italy, one of the travelers was suffering from stomach bloating, and the host helped cure her with a diet of miso. (I'm not saying you should go Workawaying if you're ill—this traveler's mother also came to oversee everything—but still, you never know what you'll find).

WoIsango.com

You should also probably be willing and able to actually work at your Workaway. These aren't vacations, and some hosts will be stricter and less forgiving than others regarding your work ethic. If you're someone who has no experience with difficult farm work, for example, it might not be a good idea to do a Workaway on a farm.

How to Choose a Host

The Workaway website boasts a truly overwhelming number of hosts. You can narrow your search down by location, but you can also search key terms that can help guide you in the right direction. You might search "music," for example—that's how I found the Italy location. You'll find hosts in busy cities and in the most remote mountains of India; you'll find opportunities to tutor and explore. You'll find shadiness, too, so trust your instincts.

Take time to actually read the host's entire bio before reaching out. Read all the comments, too, and if you're nervous or a first-timer, only reach out to hosts who have exclusively glowing reviews. I had the best experiences with hosts that had left extremely detailed bios—that showed me they were likely going to be dedicated hosts.

I also chose hosts whose bios gave me a good feeling, something like a spark of electricity or recognition. This instinctual method might not work for everyone, but it certainly led me in the right direction in all of my Workaway experiences. My Workaways gave me some of the best memories and deepest relationships of my life, and that was partly thanks to the fact that I chose places that were good fits for me.

For example, I chose to stay alone with a wizened academic in France. Something about his bio and descriptions resonated with me enough to trust him. (I also read some of his many thousand-page-long treatises on peace and compassion and decided that if someone could write this and be a psychopath, this wasn't a world I wanted to live in anyway). It was the right decision—and the two weeks I spent there were some of the most enlightening of my entire life.

When you reach out to a host, particularly if it's someone you really want to stay with, it's a good idea to frame your initial contact email as a cover letter of sorts—make sure you explain who you are and personalize your letter to fit each host.

A Workaway painting experienceWorkaway

Travel Safely

Especially if you're traveling alone, it's always a good idea to choose a host whose page has tons of good reviews. Aside from that, a quick Google search and a scan of any social media pages related to your potential host can't hurt.

Ultimately, Workawaying requires a certain amount of trust and faith on both the host and the traveler's parts—you're either trusting someone to stay in your home or trusting a stranger to host and feed you.

But that trust, in my experience, also results in rapid and deep connections unlike anything I've experienced in the "real world." When you go and share a home with someone, you're also sharing yourself with them, and in that exchange there are the seeds of a powerful bond.

Participate Fully

Wherever you go, you'll want to open your mind and participate fully. Adjust yourself to your host's lifestyle, not the other way around, and take time to get to know your host and the others around you.

You might find that you become someone you never knew you were. As a lifelong introvert, I somehow managed to develop close relationships with many of the people I was staying with.

This might be because most people who are at Workaways are seeking something for one reason or another. In my experience, you find lots of people who are at junctures in their lives, seeking connection and meaning. With the right Workaway, you might just find it.

The Broke Backpacker - WorkawayThe Broke Backpacker